91421-42-0 Rubitecan AKSci M884
 
 
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  M884    AKSci Reference Standard
Rubitecan, 99% (HPLC), powder
 
9-Nitrocamptothecin
9-nitro-20(S)-camptothecin
Orathecin
IDENTITY
CAS Number:91421-42-0
MDL Number:MFCD06656294
MF:C20H15N3O6
MW:393.35
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:99% (HPLC), powder
Physical Form (at 20°C):Solid
Melting Point:268-275°C
Optical Rotation:+36.0° - +42.0° (c=0.4, CHCl3:MeOH=8:2)
Long-Term Storage:Store long-term in a cool, dry place
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Application(s):Topoisomerase inhibitor

REVIEW
 Rubitecan is a camptothecin analog. Like other camptothecins, its antitumor activity is mediated through its inhibition of DNA topoisomerase I. It exists in equilibrium as 9-nitro-camptothecin and 9-amino-camptothecin. Both structures contain a lactone ring required for optimal activity; the carboxylic acid open-ring forms are significantly less active or inactive. A more acidic environment favors the lactone ring structure, whereas neutral or basic conditions favor the conversion to the carboxylic acid.

REFERENCES
[1]Pantazis P, Han Z, Balan K, Wang Y, Wyche JH.Camptothecin and 9-nitrocamptothecin (9NC) as anti-cancer, anti-HIV and cell-differentiation agents. Development of resistance, enhancement of 9NC-induced activities and combination treatments in cell and animal models. Anticancer Res. 2003 Sep-Oct;23(5A):3623-38.
[2] Phase II study of rubitecan, an oral camptothecin in patients with advanced colorectal cancer who have failed previous 5-fluorouracil based chemotherapy.Patel H, Stoller R, Auber M, Potter D, Cai C, Zamboni W, Kiefer G, Matin K, Schmotzer A, Ramanathan RK.Invest New Drugs. 2006 Jul;24(4):359-63.
[3] Clark JW.Rubitecan.Expert Opin Investig Drugs. 2006 Jan;15(1):71-9. Gao, Mingzhang; Bioorganic & Medicinal Chemistry Letters 2005, V15(17), P3865-3869
[4] Chen J, Hu RR, Yang XX, Gu W, Tian R, Gong F, Luo L, Fang F, Chen ZP, Cai BC. Antitumor efficacy, toxicity and pharmacokinetics of 9-nitrocamptothecin: role of lactone ratio. Cancer Chemother Pharmacol. 2013 Oct;72(4):925-9.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501

Current as of May 10, 2024

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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CATEGORIES
 APIs and Bioactives > Chemotherapeutics


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